期刊
ORGANIC LETTERS
卷 21, 期 19, 页码 7976-7981出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02961
关键词
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资金
- Rutgers University
- NSF [CAREER CHE-1650766]
- NSF-MRI grant [CHE-1229030]
- Wroclaw Center for Networking and Supercomputing [WCSS159]
Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.
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